Hydrofluoric Acid → (S)-2-methyl-4-methylidene-3-(2-propynyl)cyclopent-2-ene-1-ol

3 To a solution of (S)-2-methyl-4-methylidene-3-(2-propynyl)-1-tert-butyldimethylsilyl-oxycyclopent-2-ene (7.52 g, obtained above) in tetrahydrofuran (50 ml) was added a solution mixture (30 ml) consisting of tetrahydrofurane solution (80 parts) of 1M tetrabutylammonium fluoride and 46% hydrogenfluoride (3 parts) under ice-water cooling. The solution was then stirred at room temperature for 14 hours. The reaction solution was poured into ice-water, and then extracted with ether (150 ml ×2). The ether layers were combined, and washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resultant residue was subjected to silica gel column chromatography (eluent; n-hexane: ethyl acetate=2:1) to afford the desired product (S)-2-methyl-4-methylidene-3-(2-propynyl)cyclopent-2-ene-1-ol (3.40 g, yield 81.0%) as a pale yellow oil.

1. extractionextracted with ether (150 ml ×2)
2. washwashed with brine
3. dry with materialdried over anhydrous sodium sulfate
4. customThe solvent was evaporated under reduced pressure

ORD record

ord-2cba5950758a46bca86ca1d079b0f0c3

Source dataset

uspto-grants-1996_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05550260